(2-amino-4-phenylthiophen-3-yl)(phenyl)methanone | 52824-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-4-phenylthiophen-3-yl)(phenyl)methanone
• 英文别名: (2-Amino-4-phenylthiophen-3-yl)-phenylmethanone
• CAS: 52824-68-7
• 化学式: C₁₇H₁₃NOS
• 分子量: 279.362
• InChiKey: MKCYHOPIUHAMMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 sodium hydrogen sulfide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以157 mg的产率得到(2-amino-4-phenylthiophen-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Allosteric Modulators of the Adenosine A₁ Receptor: Synthesis and Pharmacological Evaluation of 4-Substituted 2-Amino-3-benzoylthiophenes

  摘要：

  A series of 4-substituted 2-amino-3-benzoylthiophenes was screened using a functional assay of A A(1)AR-mediated phosphorylation of ERK 1/2 in intact CHO cells to identify both potential agonistic effects as well the ability to allosterically modulate the activity of the orthosteric agonist, R-PIA. More detailed concentration-response experiments were subsequently performed on two compounds (9a and 9o) utilizing both the ERK 1/2 assay as well as a second assay of [S-35]GTP gamma S binding to activated G proteins.

  DOI：

  10.1021/jm9002582

文献信息

• [EN] A1 ADENOSINE RECEPTOR ALLOSTERIC ENHANCERS<br/>[FR] AMPLIFICATEURS ALLOSTÉRIQUES DES RÉCEPTEURS DE L'ADÉNOSINE A1
  申请人：UNIV MONASH

  公开号：WO2009049362A1

  公开（公告）日：2009-04-23

  The present invention relates generally to chemical compounds and methods for their use and preparation. In particular, the invention relates to chemical compounds which may possess useful therapeutic activity for treating conditions where the promotion of angiogensis (blood vessel formation) is beneficial, use of these compounds in therapy and the manufacture of medicaments as well as compositions containing these compounds.

  本发明一般涉及化合物及其使用和制备方法。具体地，本发明涉及可能具有有用的治疗活性的化合物，用于治疗促进血管生成有益的疾病，这些化合物在治疗中的使用以及药物的制造，以及含有这些化合物的组合物。
• Reaction Pathways to 2-Aminothiophenes and Thiophene-3-carbonitriles
  作者：Luigi Aurelio、Bernard L. Flynn、Peter J. Scammells

  DOI：10.1071/ch09004

  日期：——

  Over the past two decades 2-amino-3-benzoylthiophenes have been found to act as allosteric enhancers of the adenosine A1 receptor (A1AR). As such, compounds of this type have potential applications in the therapy of a variety of disorders by enhancing A1AR activation. Initial studies in this field identified various 2-amino-3-benzoylthiophenes as potential leads and of these PD 81723 1a has become the benchmark for comparative studies due to its favourable ratio of allosteric enhancement to antagonism. Surprisingly the synthesis and characterization of PD 81723 1a has not been previously reported. Herein we report the synthesis and characterization of this important A1AR allosteric enhancer. As part of this study we also found an unexpected reaction pathway to 2-phenylthiophene-3-carbonitriles.

  在过去的二十年里，人们发现 2-氨基-3-苯甲酰基噻吩可作为腺苷 A1 受体（A1AR）的异构增强剂。因此，这类化合物通过增强 A1AR 的活化作用，在治疗各种疾病方面具有潜在的应用价值。该领域的初步研究发现了多种 2-氨基-3-苯甲酰基噻吩类药物作为潜在的先导化合物，其中 PD 81723 1a 因其异构增强与拮抗作用的良好比例而成为比较研究的基准。令人惊讶的是，PD 81723 1a 的合成和表征以前从未报道过。在此，我们报告了这种重要的 A1AR 异构增强剂的合成和表征。作为这项研究的一部分，我们还发现了一种意想不到的 2-苯基噻吩-3-甲腈反应途径。